1-Hydroxybenzotriazole → HCID 59784092, compound

https://huagongshe.com/reaction/2079762

Participants

Role	Name	HCID	Charge
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 2733084	—
Reactant	(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid	HCID 7009590	—
Reactant	HCID 59784095	HCID 59784095	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 59784092	HCID 59784092	89%

Reaction Steps

Amine 5 (12.57 g, 25.5 mmol) is then coupled with BOC-N-methyl-L-alanine (5.18 g, 25.5 mmol) using DIEA (22.3 mL, 0.13 mol), HBTU (10.64 g, 28.1 mmol) and HOBt (3.79 g, 28.1 mmol) in DMF (550 mL) under the same conditions as in step 1 above. Purification is carried out by flash chromatography on silica gel (CH2Cl2 as eluent initially, followed by 50% Et2O/CH2Cl2 to elute the desired product). The desired coupled product 6 is isolated as a white foam (15.30 g, 89% yield): 1H NMR δ (CDCl3) 7.28-7.38 (br m, 5H), 7.03-7.19 (br m, 4H), 6.73 (br s, 1H), 6.02-6.35 (br m, 1H), 5.05-5.26 (br m, 4H), 3.84-4.82 (br m, 5H), 2.68-3.56 (br m, 9H), 1.70-2.07 (br m, 5H), 1.47 (s, 9H), 0.60-1.33 (br m, 8H); LCMS (APCl+) 679.0 (MH+), 579.0 (MH+-BOC, 100%); HPLC(C18 column) 99.4%.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07932255B2
Source dataset	uspto-grants-2011_04
ORD ID	ord-4a8704297203435785814dcbf67a79cd
Source note	uspto-grants-2011_04